


Wholly Hypothetical, Mind You

by ettieeggyo



Category: Gossip Girl
Genre: F/M, They talk too much, but ya know, hes not gossip girl, idk they drunk, takes place in a convenient yet non-specified ‘what if’ gap in Season 4, ‘dan is not Gossip Girl’ is a pretty useless tag
Language: English
Status: Completed
Published: 2019-06-12
Updated: 2019-06-12
Packaged: 2020-05-02 04:54:37
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,110
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19192222
Author URL: https://archiveofourown.org/users/ettieeggyo/pseuds/ettieeggyo
Summary: Dorota had started to notice a pattern recently: a nervous (yet elegantly dressed) Dan Humphrey turning up in the foyer of the Waldorfs’.





	Wholly Hypothetical, Mind You

**Author's Note:**

> turns up 7 years too late with too many unfinished drafts spilling out of my laptop, and a sheepish smile on me face

She’s tipsy. Dan can tell because she’s putting a finger to his lips every second word, shaking her head with eyes closed tight. She doesn’t want him to speak. Somehow drunk Blair is even more blunt than before. “You! Talking. Why? Not your turn. Shush.” He chuckles breathily onto her pressed fingertip, as her face shifts on each word: acknowledgement to anger to confusion to deliberation. It’s hard to tell if she’s flushed or blushing. 

They’re sitting in the Brooklyn loft, switching between Audrey and Katherine Hepburn only to find themselves at Nora Ephron. Harry is halfway through meeting Sally for the third time before they have given up on watching. Blair’s eyes had burned midway through the first 5 minutes and teetered on the edge of tears. She scrunched her face so often to quell them that Dan thought she was sneezing. “Have you got a cold, Waldorf?”

“No.” Blair glared at him. Dan stifled a laugh. “You are so giggly, Brooklyn.”

Dan shrugged with a smug smile. The Humphrey brand. The smug smile that said, “I survived this long, you honestly think I care what you think of me?” Or did he actually say that? Did those words come out of his mouth or did he say it without saying anything at all? Usually when Dan would say those unspoken words it was to be a smartass. But now it felt so... sad. So alone. 

“You think you’re better than me, don’t you Humphrey?”

“I am desperately trying to get into the habit of thinking nobody is better than anyone.” Dan puffed out a breath, considering slowly and carefully. As carefully as he could anyway. “You? Prime example of that. No doubt I thought you were a hardass, and yeah... you still are-”

“Hey. Hey.” She jabs a finger into his chest twice for emphasis (a slightly offended ‘Ow?!’ flies her way) and she sits up straight. “I can think of bad stuff for you too. 1? Brooklyn. Eugh. 2? Hipster. I mean, flannel and vinyl? 3-”

“While I would love to hear you list my flaws? Not my point. Don’t get sidetracked.”

“I won’t if you don’t.” Blair sneers and she is glad to see he sneers back. Their faces are so close she could have sworn that their sneering made their noses brush. She leans back from him, shifting as far back as she can without seeming off. She looks away as she sips at her hastily made G&T. 

“You are a hardass. But!” Dan raises a finger. Blair looks like a confused fish as she glances from his fingertip to his eyes and back again. Had Dan been in a worse state he would definitely have commented on it, but for now he let it be. This was important, don’t get sidetracked. “But... Blair Waldorf. You are my best friend.”

“Nate?”

“Hmmmm...” Dan considers. “I mean he tried to sleep with my little sister, so that’s a big no-no.”

“Sleeping with Jenny Humphrey would always be ‘a big no-no’, no matter what context.”

Dan ignores her. “So despite your jabs at my sister - which I do not appreciate, yes, thank you for looking slightly ashamed - Blair Waldorf. You are my friend. My best friend. Bestest. Yeah, my betstest friend.”

For some reason, when he says those words it stings. If he’d said that a year ago, she would have been hurt by the idea that she could even be associated with him. But this is a different kind of sting. It reminds her of the holiday in Nice she took at age 7, when her mother had to treat a bee sting and a baby jellyfish sting in the same day. How different, yet equally sore and irritating they had both felt. 

Blair peers at Dan from the rim of her glass, disappointed at the pitiful amount of gin and tonic left. She’s in Brooklyn with Dan Humphrey and enjoying it. There isn’t enough alcohol for this situation. “Someone is in denial.” She sing-songs quietly to herself. 

“Denial?” Dan scoffs, because of course he hears her. “Pfft, I don’t- denial of what?” Dan is shaking his head too much, muttering denial under his breath as if he were casting a curse. But odder still, was how he thought she was talking to him. 

“I wasn’t talking about you.”

He blinks. His hair somehow blinks with him. His hair is too bouncy, like a cartoon cloud. Dan often looks cartoonish to Blair. Round, wide open eyes, features just a bit too pointy. She’s not used to it. She’s used to the men of the Upper East Side - warm, sunny complexions and the mouths of sailors. Rounded features and a rose in hand. 

The kind to declare, ‘I know we just met two weeks ago, but I cannot stand here a second knowing we are not yet married.’ They’d buy their pretty, little girlfriends expensive jewellery every opportunity possible, dedicate a building in their name so they are immortalised in New York City forever. Tears would stream down their cheeks in joy as they’d answer, ‘yes, yes, of course, what other choice is there, you silly man?’ against their lips. Blair had watched that type of love happen a dozen times, she’d even tried to orchestrate that type of love a dozen times. 

Dan was so far from that, it was embarrassing. He was the type she’d catch eating cereal out the box dry, wearing nothing but boxers and a shirt with a mole dressed as Robin exclaiming, “Holy Moley, Batman!”. He left that shirt at hers once, after he stayed overnight. She hates that shirt. Hates it. She’d ask Dorota to burn it if it didn’t make such a comforting pillow cover. He’s the sort that her mother orders to fetch her a drink, only for her to realise after he brought her the second Bloody Mary of the evening, that she didn’t hire a cater waiter. But he’s too generous and respectful to even complain about the confusion. 

Dan doesn’t have a lot of money, but he makes good coffee. He can’t buy expensive jewellery, but he did get her a silly plastic key-ring in the shape of a crown from a claw machine at the fair. He doesn’t really like roses all that much, or any plant that isn’t a set of tiny cacti. He doesn’t ask her to run away with him in a moment’s notice, but she knows he’d go anywhere with her if she asked. In fact he doesn’t ask much of her at all. 

“You’re nothing like Chuck.” Blair ponders aloud.

“Thank you, you have no idea how much that means to me.”

She slaps him on the arm and he laughs. “Don’t say that so sincerely, Humphrey! Besides, I just mean exterior... exterior-wise.”

“Exterior-wise?”

“You don’t look alike, okay? Chuck is all, square face and you’re more hexagonal. You would be square face were it not for those cheekbones... It makes you look like a chipmunk.”

Dan leans forward into her personal space, smiling. Normally she’d want him gone, to sit back and away from her. She had made the effort of moving away from him, after all. But the smell of craft IPAs and shaving cream is somehow comforting now. Is that grapefruit wafting off his neck? Silly, little, sharp-edged chipmunk man. “I have no idea what you’re on about, Blair.”

“Say, hypothetically,” Blair frowns, exaggerated to such a degree that it’s slightly comical. Dan wants to kiss the frown off his best friend. Except, he doesn’t. Except, yes, he really does and he feels dangerously close to her face again. “And this is purely, wholly hypothetical, mind you-”

Dan raises a hand like a Boy Scout. “Noted.”

“And that’s good! Because this is the stupidest question or request or whatever, that I will ever ask.” Blair sighs, she’s resigned and not looking straight at him. “Would you ever take me on a date?”

“You? As in- you? You, in specific?”

For someone with a face so soft, her pursed lips and pinched cheeks could be sharp. Dan supposes that she’d learnt to be. Blair is poised, but because Dan is the exact opposite she tends to be less so in his presence. 

Dan knows for example, that whatever strap-sleeved dress she wore to Brooklyn tonight is probably the cheapest she has in her wardrobe - what can he say, he picked up some fabric knowledge from Jen’s seamstress antics. He also knows that with him Blair doesn’t wear perfume around him in private, or do her hair in any fancy updos that only a professional (read: paid) stylist would opt to do willingly. The most dramatic makeup he has seen on her was a dash of mascara and a quick dab of lip gloss. It’s very unlike her. 

She turns to face him then, a scowl on her lips. “What other kind of ‘me’ is there?”

“Well, I don’t know!” Dan exclaims, exasperated. “There are several different- look, are we talking us in high school or us now or us in the future-”

“Your sister clearly indulged your habit of overthinking to a severe degree, if this is the response I get right now.” Blair knew how to be sardonic. It used to be mean, but now it was mostly just hot. Dan couldn’t deny that he likes to picture kissing her up and down her neck, leading to her collarbone and the top of her breasts and eventually even further down, until she was gasping and saying breathily in that exact same sardonic tone, “Wow, Dan. I find you so irresistibly unattractive. You really don’t know how to turn me on. Keep going.” 

In his defence, dialogue wasn’t exactly what his writing was known for. He much preferred descriptive narrative prose. Either way, Dan needed to question the inner workings of his sexuality one day. Not now, though. 

“Nothing to say to that?” Blair waved a hand in front of his face and he jumped. “I’m just confused, okay?”

“Why are you confused?”

“Serena fell for you instantly. You slept with several girls over the summer after you broke up - for the first time. Slept with Georgina. Horrendous. Dated a movie and television star. Had a threesome with said movie and television star-”

“And you keep track of my love life... because...?” Dan held a quizzical expression on his face. 

“Because it makes no sense!” Blair exclaimed. She slumped backwards against the ratty sofa, only to find a sock stuffed between the pillows. She plucked it with a disgruntled air and a twisted nose before she shoved it in Dan’s face (“Aagh, Blair! Why?”). She threw her hands up to the air as she glared at him. “This! This is what I’m talking about.”

“A smelly old sock?”

“Yes! And also no!” Blair doesn’t know why she’s yelling. 

“Why are you yelling?”

“I don’t know!”

“Can you stop?”

“No!”

“Okay then!”

“Your life is like this smelly old sock that you haven’t washed. And yet, despite all odds, people are into it. You are attracting attention from-” Blair lifts a hand to count on her fingers “-Serena, Georgina, Vanessa, Olivia, random bimbos, probably Nelly Yuki too, and the fact that I am joining that list is-” She clasps her hands to her mouth. 

“Wait... a minute.” Dan smiles smugly. Blair is beetroot red in the face and looks close to throwing up. She’s not looking at him. “Wholly hypothetical, huh? Was that a thinly, perhaps even terribly, veiled way of seeing if you want to ask me out?”

Blair doesn’t answer. She doesn’t leave either. She just sits there still as a Vogue model on a magazine cover. A very flushed, drunk and embarrassed Vogue model. Dan sucks his lips inwards, only to pop them open again. No response. Still as a mannequin. He presses play on the movie. Besides the outside noise of Brooklyn traffic with fellow drunkards tossing bottles on the street and the inside noise of the movie, it’s silent. 

Dan wants to understand Blair more. In her silence he finds a depth he falsely perceived as shallow. For once, he says with all sincerity and none of the disappointment, “You’re not who I thought you were.”

“You used to think little of me didn’t you.” Blair says softly. 

“And you didn’t think the same of me?” 

“I thought you...” Blair starts, but finds herself too ashamed to finish. “We all turned against each other eventually. You were just caught in the crossfire-”

“Blair.”

“Don’t make me say it.” Blair winces. Dan still expects an answer anyway. “Fine! I never want to admit that I actually kind of like you because you’re you, but I don’t want to admit that I definitely hated you because... well, you’re you. You’re Dan. You make ridiculous puns about Victor Hugo and cappuccinos with my initials dusted on them. You make me laugh, when I’d almost forgotten how. But you also hated me, and I hated you.”

“And you’re Blair.” Dan responds. “You schemed and you lied and you were good at it-”

“I thought this was supposed to be a set of compliments!” Blair bites.

“I’m getting there!” Dan bites back. “But all of that, it made you cunning and clever and... so intuitive. You’ve seen me at my worst, and still decide to waste your time with me. You’re immensely strong and persistent, which as much as it makes you a pain, it also makes you my favourite challenge. You’re my best friend.”

“We’re supposed to hate each other.”

“So you keep saying.”

And it’s only when Harry finds himself running to meet Sally at the New Year party that Blair dares to admit it to herself.

“Okay,” Blair sighs and presses pause. “Yes. I want to go on a date with you. So here goes. Dan, Do you want to go out with me?”

Dan blinks. Maybe about three times. And then one word slips out. A happy accident. She gets her answer.

———

 

Dorota could swear that she doesn’t see Blair as often as she used to. Some other drama must be occurring in her life yet again, because Daniel Humphrey likes to come up into the elevator these days. 

For him to turn up in the Waldorf establishment alone, and this often... it concerns Dorota. 

But Blair seems perfectly happy... which just adds to Dorota’s concern. 

It’s the fifth time in the past two weeks that he has turned up in the foyer. Dorota spots him standing and absently whistling, whilst she carries the remnants of Blair’s breakfast downstairs. “Mister Humphrey.” She looks him up and down, eyes narrowed. The boy jumps, and Dorota can’t deny the small satisfaction she takes in scaring him like that. Until she notices what the hand that’s not in his pockets is doing: holding flowers.

Daniel chuckles nervously, and shrugs. “I’m...uh, it’s a gift. For Serena. Nothing much, just...yeah. Nothing else behind it.”

“For Serena.” Dorota repeats, eyes narrowing further if it were even possible. 

“Yes.”

“Peonies? A curious choice.”

“Really?” Dan frowns quizzically. “I didn’t even- I can’t say that I noticed?”

“Bright pink too.”

“Well, Serena’s favourite colour.”

“I had been led to believe that her favourites are lavender. And butterscotch.”

“Hard to find flowers of that colour.”

“Lavender, perhaps? Or no flowers. Just butterscotch candies?”

“Dorota!” Blair’s voice yelled from the stair. Dorota knew her investigation into the mysterious workings of Daniel Humphrey would have to wait. “I can hear you pestering our guest from the other side of the penthouse. I need help selecting a day dress, and quickly.”

Dorota hears Dan sigh out of relief. “I mean,” He starts, rubbing the back of his neck awkwardly. “That- that sounds important.”

“Indeed.”

She trots up the stairs, deciding to leave the disaster to its own devices. Had she stayed she might have seen Dan, palm to his forehead, looking yet more flustered and embarrassed at the situation he had found himself in. “Prepare for tutus and frills, at the Saturday matinée. Your absolute favourite, Dan.” Blair had taken to calling him Dan in private and he had to say he liked how regal it sounded when she said it, whispered it, laughed with it on her lips. But only in private. They kept themselves secret, not for fear but just for fun. 

She came down the stairs barely casting a glance at him, right hand daintily clasping the bannister, and Dan was already enjoying this game they were playing. “Humphrey, what could possibly be the reason for your visit?” He’s struggling not to laugh at how stiff it sounds.

“Blair.” Dan says. He sniffs and turns his head to the side like a disgruntled aristocrat. Out of the corner of his eye, he swears he can see the corner of Blair’s mouth twitch upwards. And also Dorota looking far too confused, but that doesn’t matter. “I didn’t come to see you. Not at all.”

“Why would you? It’s not like I would want or arrange to see you.”

“Exactly. Could not agree more.” Dan smiles, and when he looks at her properly his breath catches unintentionally. But he continues the ruse. “Anyway, Chuck has gotten himself into more trouble with Bass Industries.”

“Oh dear,” Blair feigns. “And did I hear Nate is dating another woman of questionable age?”

“Well, clearly we have to interfere in their lives. Send a video tape of Chuck sleeping with that exact same woman or something similar to Gossip Girl.” Dan nods, and Blair nods her head vigorously back. “There’s no time to waste.”

“I agree.” Blair says with all the elegance and poise she can muster. “But as you can see from my dress, I do have a date that I simply have to attend later this afternoon.” 

“As do I, in fact my date even chose my suit. Got it fitted.”

“She has good taste.”

“The best.”

“Dorota,” Blair turns to her maid, who by this point has given up trying to understand the scene in front of her. “I will not be back until late. I’m afraid this may take all day, or even longer... I won’t be back until tomorrow, maybe... Don’t wait up.”

Dorota slowly nods her assent, and watches dubiously as pauper leads princess to the elevator in a scurrying manner. Dorota doesn’t miss the way his knuckles brush against hers, or how from the window in the parlour she can see their faces meet slowly in the middle, halfway. Curious, Dorota thinks to herself. Then she dusts down the bannisters, wondering how she could ever be surprised at all.

**Author's Note:**

> they will always deserve better than what they got
> 
> Edit: To all those who leave comments or kudos or both, each one boosts my day up to the moon and back - you guys are truly awesome, and tell me I am right to pursue this lost hobby of mine again. Not enough words! Thank you! :D


End file.
